Anal Sex for a beginner (Questions for Bottoms, Vers, and Tops who have Bottomed)

If you don't want to know the explaination behind this post and would like to save time, just skip down to the questions:

Ok, I am a Bicurious young kid who is fairly new to the whole gay world.I have had experiences before with gay oral sex, and I enjoy it. But I have only seen myself being able to please someone else orally. I just don't feel comfortable going all the way.

I have never gone all the way with either sex, and I always hoped my first experience with that would be in a heterosexual experience. But I am getting more and more curious about bottoming and it is starting to become an awkward fantasy in a way. (ASIDE: lol, I think my roomate is having sex in the next room, not helping!)

My hope is to abstain from full on sex until I am 1. In love and committed or 2. Married. And there are other personal issues that stop me from going all the way, but I wanted ask because it really gets me now:

QUESTIONS:

Does anal sex hurt?If so, how much pain is it as opposed to the pleasure?Is it bearable the first time or does it become more bearable as you do it more?Did you have any problems making the decision to Bottom?

And I'll also be the bearer of bad news. Especially if your first time is with someone 25 and under, it's gonna hurt. When you're with yourself you can control but your first few times aren't a good measure of whether or not it's for you. The very first time I had sex I cried and begged him to stop and swore off bottoming for eternity. But flash forward to now and I am a total bottom and love it.

Does anal sex hurt?If so, how much pain is it as opposed to the pleasure?Is it bearable the first time or does it become more bearable as you do it more?Did you have any problems making the decision to Bottom?

1. Yeah it hurts but in a good way.

2. At first more pain than pleasure.

3. It's bearable if it is small but the first time is gonna hurt. Hopefully the top will ensure that it goes as smooth as possible.

4. Yes. Bottoming is not just physical, it's a mental act of submission too. That was the hardest part for me - letting someone else take control. That's why I made my first bf use toys a couple times. When I bottom I still like to be on top - I just can't give up total control!

Only if it's not done right - if you're not warmed up enough, if the top goes too fast too soon, if you tense up (you must be relaxed, inside and out) or if you don't use sufficient lube.

TreBack saidIf so, how much pain is it as opposed to the pleasure?

If it hurts, you'll know it - if the top goes in too deep too soon you will get what I would call a 'ring sting' where you cause pain to one of the internal sphincters, this will REALLY hurt for a minute or so - get that dick out of you immediately and wait until the pain subsides. If you're fucked really hard it can sometimes hurt as well, but that can be a turn on for some bottoms - just listen to your body and try and gauge your limits, you don't really want to be ripped open or limping for days after sex.

TreBack saidIs it bearable the first time or does it become more bearable as you do it more?

The first time is probably the most difficult as it's a new experience and you need to learn how to bottom well, if you have a decent top they should make it pleasurable for you but you can increase your odds of a good experience by practicing with fingers and sex toys before you get fucked by an actual cock. Experiences vary massively - I'm mainly a top but the first time I got fucked it was actually fine, the guy topping me knew what he was doing and it didn't really hurt.

TreBack saidDid you have any problems making the decision to Bottom?

I think it's one of those things where you quickly find out which side your bread is buttered (or even both sides) through trial and error. You could be a total bottom, a total top, or somewhere on the scale. Don't ever do anything you're not comfortable with and make sure whoever your sex partner is, they know the boundaries, your limits, and what the expectations are before you get naked!

It did hurt the last time. It feels okay, other times not but maybe because I was never completely relaxed. Depends on your mood.

TreBack saidIf so, how much pain is it as opposed to the pleasure?

Last time was pure pain. You must be careful, I ended up with a fissure of moderate severity. You don't want that.

TreBack saidIs it bearable the first time or does it become more bearable as you do it more?

You get used to it with time, so it generally becomes more bearable I'd say.

TreBack saidDid you have any problems making the decision to Bottom?

I have problems making the decision to bottom. Because of my past experience, I ended up with an injury. Now it's healed, but I ended up with scars. I'd bottom if the other guy were patient and understanding, my previous guy was persistent and told me he wouldn't hurt me. I also have problems because I can't "get off" when someone's inside me like that.

No it does not hurt, but only if you do it properly. You have to do prepwork. You can't just bend over and expect it to go in easily. You gonna wash the area, work a finger in there, progressively relax the sphincter. Take your time.Pleasure, pleasure, pleasure, OMFG PLEASURE!!!First time was okay.No problems with making a decision.

The biggest fkn thing people left out was.. DOUCHE!That's why alot of people's first bottoming experience is horrible because they paint Picasso's and make chili specials on dicks. Buy a fleet Enema dump the saline water out and use regular water.Make sure the waters clear that your fleeting out. That's how to judge if your bowels are clean for heavy duty action.

I haven't had anal before, but I love to anally masturbate. Im sure that helps to get used to it.

Also when you insert for the first time in a while, just put it in a centimeter, then remove it. Repeat until your anus is relaxed enough to take it in the whole way. Definitely makes it feel good when I use toys XD

You have gotten some good advice here on bottoming in anal sex. A few more tips: Get a copy of the book "the joy of gay sex." (Amazon) A bit dated but with lots of useful information. Since you do not want to have sex until you are in a committed relationship, it will probably be a while. In the meantime, get a copy (rent?) of the original, British TV series, Queer as Folk. Pay careful attention to the first episode (I believe) where the main character takes the 15 year old boy to bed for the first time. That is something you will want someone to do to you. Buy online, or at a sex shop, or adult bookstore a dildo and a vibrator. The vibrator will come in handy if you'd ever go with women, since it drives them crazy. Unless it is specifically designed for a lesbian, a vibrator normally comes in the shape of a penis. Before you are looseend up enough to plunge a dildo in all the way, you can use the vibrator around and in your anus to get you all excited. When you graduate to going "all the way", as you put it, with another real person, your partner could sometimes incorporate the use of the vibrator into your sexual repertoire. When you use a dildo, you get to control totally how deep it goes in, how slowly it enters, and how fast you eventually move it. Practice enough, and you will have become totally used to being fucked, before you ever have a real dick inside you. Have fun.

I'm getting into bottoming too. I've done it before but I guess I'm becoming more vers. Anyway, my issue isn't taking it. If I want to bottom, I really want to bottom. Plus, I've topped enough to know that the bottom has to relax and just want the dick, so that part is out the window.

My biggest concern is always cleanliness. My ass gets a thorough the rinse, but I won't totally let go until he has drilled me, pulled out, and the condom is still clean. And what if he's bigger and does get up into the other areas? Now, I'm just paranoid and wouldn't try a dick bigger than a certain length.